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Am. Chem. Soc. 103, 2483 (1981). 6 3 . Β . M . T r o s t a n d W . H . P e a r s o n , J. Am. Chem. Soc. 105, 1054 (1983). 64. A . D . B a r o n e a n d D . S. , 3673 (1978). 2 Vinyl Azides and Nitrenes Alfred Hassner Department of Chemistry State University of N e w York at Binghamton Binghamton, N e w York I. I n t r o d u c t i o n I I . S y n t h e s i s of Vinyl A z i d e s A . I n t r o d u c t i o n of t h e A z i d e F u n c t i o n o n t o C = C . B . F o r m a t i o n of t h e C = C B o n d in t h e P r e s e n c e of t h e Azide Function C.
B a r o n e , D . L . S n i t m a n , a n d D . S. W a t t , ibid. 4 3 , 2066 (1978). 17. P . M a r g a r e t h a , S. Solar, a n d Ο . E . P o l a n s k y , Angew. Chem. Int. Ed. Engl. 10, 412 (1971). 18. a. J. A . , 2959 (1975); b . H . Q u a s t a n d B . Seiferling, Liebigs Ann. , 1566 (1982). 19. Μ . B . F r a n k e l a n d D . O . W o o l e r y , J. Org. Chem. 48, 611 (1983). 20. E . P . K y b a a n d R. A . A b r a m o v i t c h , / . Am. Chem. Soc. 102, 735 (1980). 2 1 . a. G . G e i s e l e r a n d W .
3 Ar-CH CH C0 Et 2 2 II (Ar-CH—CH-C0 Et) L OH 0 95 NaOEt 2 97 96 Ar-CH=C-C0 Et I 9 ά N 3 98 B e c a u s e of the p r e s e n c e of strong b a s e , the structure of the a l d e h y d e is restricted to o n e in w h i c h a p r o t o n s are absent, namely, an aromatic and h e t e r o a r o m a t i c a l d e h y d e . S o m e interesting e x a m p l e s of 98 w e r e provided b y the g r o u p s of H e m e t s b e r g e r (32) and R e e s (33). , 99 —> 100 —> 101). 2. , 102 —» 103). T h e stereochemistry of the p r o d u c t is usually t r a n s .